WO2005037810A3 - Cyclopropyl methanone derivatives, the preparation and the therapeutic use thereof - Google Patents

Cyclopropyl methanone derivatives, the preparation and the therapeutic use thereof Download PDF

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Publication number
WO2005037810A3
WO2005037810A3 PCT/FR2004/002637 FR2004002637W WO2005037810A3 WO 2005037810 A3 WO2005037810 A3 WO 2005037810A3 FR 2004002637 W FR2004002637 W FR 2004002637W WO 2005037810 A3 WO2005037810 A3 WO 2005037810A3
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WO
WIPO (PCT)
Prior art keywords
group
alkyliden
aminocycle
necessary
preparation
Prior art date
Application number
PCT/FR2004/002637
Other languages
French (fr)
Other versions
WO2005037810A2 (en
Inventor
Martin Juan Antonio Diaz
Arenales Beatriz Escribano
Escudero Perez Ulpiano Martin
Original Assignee
Sanofi Aventis
Martin Juan Antonio Diaz
Arenales Beatriz Escribano
Escudero Perez Ulpiano Martin
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0312139A external-priority patent/FR2861072B1/en
Priority claimed from FR0408807A external-priority patent/FR2874215B1/en
Application filed by Sanofi Aventis, Martin Juan Antonio Diaz, Arenales Beatriz Escribano, Escudero Perez Ulpiano Martin filed Critical Sanofi Aventis
Publication of WO2005037810A2 publication Critical patent/WO2005037810A2/en
Publication of WO2005037810A3 publication Critical patent/WO2005037810A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Abstract

The invention relates to a compound of formula (I), wherein n ranges from 1 to 6, A is aryl such as phenyl or naphtyle, or monocyclic heteroaryl such as thienyl, furyl or pyrrolyl; aryl or heteroaryl being substituted, if necessary; B is *NR1R2, wherein R1 and R2 represent independently from each other a C1-6 alkyl group, or R1 and R2 represent together a C2-6 alkyliden group, C1-3 alkyliden-O-C1-3 alkyliden group, or C1-3 alkyliden-N(R3)- C1-3 alkyliden group wherein R3 is a hydrogen atom, a C1-3 alkyl or C1-6 alkylcarbonyl group, or * an aminocycle such as aziridine, azetidine, pyrrolidine, piperidine bound to a O-(C)n group by aminocycle carbon; the groups R1, R2 and aminocycle being, if necessary and the O-(C)n group represents a O-C1-6 alkyliden if necessary substituted group. Said invention can be used for therapy.
PCT/FR2004/002637 2003-10-17 2004-10-15 Cyclopropyl methanone derivatives, the preparation and the therapeutic use thereof WO2005037810A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0312139A FR2861072B1 (en) 2003-10-17 2003-10-17 CYCLOPROPYLMETHANONES DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF
FR0312139 2003-10-17
FR0408807 2004-08-11
FR0408807A FR2874215B1 (en) 2004-08-11 2004-08-11 CYCLOPROPYLMETHANONES DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF

Publications (2)

Publication Number Publication Date
WO2005037810A2 WO2005037810A2 (en) 2005-04-28
WO2005037810A3 true WO2005037810A3 (en) 2005-07-07

Family

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PCT/FR2004/002637 WO2005037810A2 (en) 2003-10-17 2004-10-15 Cyclopropyl methanone derivatives, the preparation and the therapeutic use thereof

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AR (1) AR046116A1 (en)
TW (1) TW200524859A (en)
WO (1) WO2005037810A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101400407A (en) * 2006-03-10 2009-04-01 纽约州州立大学研究基金会 Tropane prodrugs with central nervous system activity

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523302A (en) * 1993-11-24 1996-06-04 The Du Pont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
WO2003048096A1 (en) * 2001-12-05 2003-06-12 Aventis Pharma S.A. Substituted aryl-cycloalkanes, and use thereof as anticancer agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5523302A (en) * 1993-11-24 1996-06-04 The Du Pont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
WO2003048096A1 (en) * 2001-12-05 2003-06-12 Aventis Pharma S.A. Substituted aryl-cycloalkanes, and use thereof as anticancer agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BRAVO,P. ET AL.: "Oxygen Heterocycles by Sulphur Ylide Annulation. The Reaction of Dimethylsulphoxonium Methylide on ortho-Hydroxybenzal Ketones; A Case of Annulation Leading to a mixture of unexpected Oxygen Heterocycles", GAZZ. CHIM. ITAL., vol. 114, no. 3, 1984, pages 93 - 102, XP009029494 *
DONNELLY ET AL.: "Cyclopropyl Epoxides. Reactions of Some alpha,beta- Dibromoketones with Dimethyloxosulphonium Methylide", J.CHEM.SOC.PERKIN TRANS 1, 1979, pages 2629, XP009029527 *
MURPHY W S ET AL: "Reactions of aryl cyclopropyl ketones. A new synthesis of aryl tetralones", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 11, 1981, pages 2920 - 2926, XP002211055, ISSN: 0300-922X *

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TW200524859A (en) 2005-08-01
WO2005037810A2 (en) 2005-04-28
AR046116A1 (en) 2005-11-23

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